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2D Structure
Also known as: 22916-47-8, Monistat, Monistat iv, Daktarin iv, Miconazol, Miconazolo
Molecular Formula
C18H14Cl4N2O
Molecular Weight
416.1  g/mol
InChI Key
BYBLEWFAAKGYCD-UHFFFAOYSA-N
FDA UNII
7NNO0D7S5M

An imidazole antifungal agent that is used topically and by intravenous infusion.
Miconazole is an Azole Antifungal.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole
2.1.2 InChI
InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2
2.1.3 InChI Key
BYBLEWFAAKGYCD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
7NNO0D7S5M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Brentan

2. Dactarin

3. Miconasil Nitrate

4. Miconazole Nitrate

5. Monistat

6. Nitrate, Miconasil

7. Nitrate, Miconazole

8. R 14,889

9. R-14,889

10. R14,889

2.3.2 Depositor-Supplied Synonyms

1. 22916-47-8

2. Monistat

3. Monistat Iv

4. Daktarin Iv

5. Miconazol

6. Miconazolo

7. Miconazolum

8. Minostate

9. Monistat-derm

10. 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1h-imidazole

11. Mjr 1762

12. Miconazolum [inn-latin]

13. Vusion

14. Florid(nitrate)

15. 1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

16. Brentan

17. R 18134

18. 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole

19. Miconazole 3

20. Nsc 170986

21. Daktarin

22. Miconazole (monistat)

23. Miconazole 7

24. Monistat 3

25. Monistat 5

26. Monistat 7

27. Monistat 1 Combination Pack

28. Chembl91

29. Monistat (tn)

30. Mfcd00216019

31. Miconazole 7 Combination Pack

32. 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole

33. 7nno0d7s5m

34. R18134 Nitrate

35. 1h-imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-

36. 1h-imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-

37. Mcz

38. Dactarin

39. Chebi:82892

40. Monistat 3 Combination Pack

41. 22916-47-8 (free)

42. Nsc-170986

43. Miconazolo [dcit]

44. Ncgc00016770-01

45. Micozole

46. Zimycan

47. 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl) Imidazole

48. Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-

49. Femizol-m

50. Miconazole-7

51. Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-

52. Monazole 7

53. 1-[2-(2,4-dichlorophenyl)-2-{[(2,4-dichlorophenyl)methyl]oxy}ethyl]-1h-imidazole

54. Miconazol [inn-spanish]

55. Oravig

56. Aflorix(nitrate)

57. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole

58. 1-{2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}-1h-imidazole

59. Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy) Phenethyl)-

60. Albistat(nitrate)

61. Andergin(nitrate)

62. Conofite(nitrate)

63. (+/-)-miconazole Nitrate Salt

64. 1h-imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) Methoxy)ethyl)-

65. Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) Methoxy)ethyl)- (9ci)

66. Monista (nitrate)

67. Micantin (nitrate)

68. Novo-miconazole Vaginal Ovules

69. Ccris 7924

70. Gyno-daktar(nitrate)

71. Lotrimin Af(nitrate)

72. Nsc169434

73. Epi-monistat(nitrate)

74. Monistat 7 Vaginal Suppositories

75. Miconazole Nitrate Salt

76. Einecs 245-324-5

77. Unii-7nno0d7s5m

78. Brn 0965511

79. Zimybase

80. Miconazole Base

81. 1-(2,4-dichloro-beta-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole

82. Sr-01000000271

83. 1-(2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

84. 1-[2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole

85. 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-1h-imidazole

86. Miconazole [usp:inn:ban:jan]

87. Prestwick_335

88. Oravig (tn)

89. Spectrum_000965

90. Miconazole [mi]

91. Miconazole [inn]

92. Miconazole [jan]

93. Prestwick0_000067

94. Prestwick1_000067

95. Prestwick2_000067

96. Prestwick3_000067

97. Spectrum2_001048

98. Spectrum3_000507

99. Spectrum4_000061

100. Spectrum5_001297

101. Dsstox_cid_3319

102. Miconazole [vandf]

103. Bmse000924

104. (+-)-1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole

105. Cid_4189

106. Miconazole [mart.]

107. Schembl2866

108. Dsstox_rid_76975

109. Miconazole [who-dd]

110. Dsstox_gsid_23319

111. Oprea1_091955

112. Bspbio_000253

113. Bspbio_002033

114. Kbiogr_000581

115. Kbioss_001445

116. Mls002222203

117. Divk1c_000156

118. Spbio_000976

119. Spbio_002174

120. Bpbio1_000279

121. Gtpl2449

122. Miconazole (jp17/usp/inn)

123. Dtxsid6023319

124. Miconazole [ep Impurity]

125. Miconazole [orange Book]

126. Schembl13934598

127. Bdbm31772

128. Kbio1_000156

129. Kbio2_001445

130. Kbio2_004013

131. Kbio2_006581

132. Kbio3_001533

133. Miconazole [ep Monograph]

134. Miconazole [usp Impurity]

135. Ninds_000156

136. Hms1568m15

137. Hms2090b21

138. Hms2095m15

139. Hms2232b14

140. Hms3374j10

141. Hms3656e14

142. Hms3712m15

143. Miconazole [usp Monograph]

144. Hy-b0454

145. Tox21_110601

146. Dl-448

147. Nsc170986

148. S2536

149. Stk834405

150. 1-(2,4-dichlorophenyl)-1-[(2,4-dichlorophenyl)methoxy]-2-imidazolylethane

151. Akos001574474

152. Akos016842489

153. Ccg-220067

154. Db01110

155. Ds-1881

156. 1h-imidazole, 1-2-((2,4-dichlorophenyl)-2-((2,4-dichlorophenyl))methoxy)ethyl)-, (+-)-

157. Idi1_000156

158. Ncgc00018294-02

159. Ncgc00018294-04

160. Ncgc00018294-06

161. Ncgc00018294-08

162. 75319-47-0

163. Miconazole 100 Microg/ml In Acetonitrile

164. Nci60_001353

165. Nci60_001380

166. Smr001307249

167. Sbi-0051448.p003

168. Cas-22916-47-8

169. Db-046018

170. Ab00053500

171. Ft-0628942

172. Sw196614-4

173. D00416

174. R18134

175. Ab00053500-23

176. Ab00053500-24

177. Ab00053500-25

178. Ab00053500_26

179. Ab00053500_27

180. Ab00053500_28

181. 216m019

182. A878389

183. Ae-641/01941016

184. Q410534

185. J-014898

186. Sr-01000000271-5

187. Brd-a82396632-001-03-0

188. Brd-a82396632-008-02-7

189. 1-[2,4dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole

190. 1-[2,4-dichloro-beta-([2,4-dichlorobenzyl]oxy)-phenethyl]imidazole

191. 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)-phenethyl]imidazole

192. 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole

193. 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole

194. Imidazole,4-dichloro-.beta.-[(2,4-dichlorobenzyl)oxy]phenethyl]-

195. 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-imidazol

196. 1-[2,4-dichloro-.beta.-[(2,4-dichlorobenzyl)oxy]phenethyl]imidazole

197. 1-[2,4-dichloro-beta-([2,4-dichlorobenzyl]oxy)-phenethyl] Imidazole

198. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole

199. 1h-imidazole,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-

200. Imidazole, 1-(2,4-dichloro-.beta.-((2,4-dichlorobenzyl)oxy)phenethyl)-

201. (+/-)-1-(2,4-dichloro-b-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole

202. 1-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1h-imidazole

203. 1-[2-(2,4-dichlorobenzyl)oxy-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric Acid

204. 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)-methoxy]ethyl]-1h-imidazole

205. 1-[2-[(2,4-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1h-imidazole #

206. Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)- (9ci)

207. 1h-imidazole, 1-2-((2,4-dichlorophenyl)-2-((2,4-dichlorophenyl))methoxy)ethyl)-, (+/-)-

208. Monistat, Daktarin Iv, Miconazolo, Miconazolum, Dactarin, Miconazol, Minostate, Brentan, Florid(nitrate)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 416.1 g/mol
Molecular Formula C18H14Cl4N2O
XLogP35.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass415.983074 g/mol
Monoisotopic Mass413.986024 g/mol
Topological Polar Surface Area27 Ų
Heavy Atom Count25
Formal Charge0
Complexity417
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 22  
Drug NameMiconazole 3
PubMed HealthMiconazole/Zinc Oxide/White Petrolatum (On the skin)
Drug ClassesAntifungal
Active IngredientMiconazole nitrate
Dosage FormCream
RouteVaginal
Strength4%
Market StatusOver the Counter
CompanyTaro

2 of 22  
Drug NameMiconazole 3 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream
RouteTopical, vaginal
Strength2%,4%
Market StatusOver the Counter
CompanyPerrigo

3 of 22  
Drug NameMiconazole 7
Active IngredientMiconazole nitrate
Dosage FormCream
RouteVaginal
Strength2%
Market StatusOver the Counter
CompanyActavis Mid Atlantic

4 of 22  
Drug NameMiconazole 7 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,100mg
Market StatusOver the Counter
CompanyG And W Labs

5 of 22  
Drug NameMonistat 1 combination pack
Drug LabelMONISTAT 3 Vaginal Suppositories are white to off-white suppositories, each containing the antifungal agent, miconazole nitrate, 1-[2,4-Dichloro--[(2,4-dichlorobenzyl)oxy]phenethyl]-imidazole mononitrate, 200 mg, in a hydrogenated vegetable oil bas...
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,1.2gm
Market StatusOver the Counter
CompanyInsight Pharms

6 of 22  
Drug NameMonistat 3
Active IngredientMiconazole nitrate
Dosage FormCream; Suppository
RouteVaginal
Strength200mg; 4%
Market StatusOver the Counter; Prescription
CompanyInsight Pharms

7 of 22  
Drug NameMonistat 3 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream
RouteTopical, vaginal
Strength2%,4%
Market StatusOver the Counter
CompanyInsight Pharms

8 of 22  
Drug NameMonistat 7
Drug LabelORAVIG (miconazole) buccal tablets are applied topically to the gum once daily and release miconazole as the buccal tablet gradually dissolves [ see Clinical Pharmacology (12.3)].Miconazole is an imidazole antifungal agent and is described chemically...
Active IngredientMiconazole nitrate
Dosage FormCream; Suppository
RouteVaginal
Strength100mg; 2%
Market StatusOver the Counter
CompanyInsight Pharms

9 of 22  
Drug NameM-zole 3 combination pack
PubMed HealthMiconazole
Drug ClassesAntifungal, Imidazole
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,200mg
Market StatusOver the Counter
CompanyActavis Mid Atlantic

10 of 22  
Drug NameOravig
Active IngredientMiconazole
Dosage FormTablet
RouteBuccal
Strength50mg
Market StatusPrescription
CompanyBioalliance Pharma

11 of 22  
Drug NameVusion
Active Ingredientpetrolatum, white; Miconazole nitrate; zinc oxide
Dosage FormOintment
RouteTopical
Strength15%; 81.35%; 0.25%
Market StatusPrescription
CompanyDelcor Asset

12 of 22  
Drug NameMiconazole 3
PubMed HealthMiconazole/Zinc Oxide/White Petrolatum (On the skin)
Drug ClassesAntifungal
Active IngredientMiconazole nitrate
Dosage FormCream
RouteVaginal
Strength4%
Market StatusOver the Counter
CompanyTaro

13 of 22  
Drug NameMiconazole 3 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream
RouteTopical, vaginal
Strength2%,4%
Market StatusOver the Counter
CompanyPerrigo

14 of 22  
Drug NameMiconazole 7
Active IngredientMiconazole nitrate
Dosage FormCream
RouteVaginal
Strength2%
Market StatusOver the Counter
CompanyActavis Mid Atlantic

15 of 22  
Drug NameMiconazole 7 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,100mg
Market StatusOver the Counter
CompanyG And W Labs

16 of 22  
Drug NameMonistat 1 combination pack
Drug LabelMONISTAT 3 Vaginal Suppositories are white to off-white suppositories, each containing the antifungal agent, miconazole nitrate, 1-[2,4-Dichloro--[(2,4-dichlorobenzyl)oxy]phenethyl]-imidazole mononitrate, 200 mg, in a hydrogenated vegetable oil bas...
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,1.2gm
Market StatusOver the Counter
CompanyInsight Pharms

17 of 22  
Drug NameMonistat 3
Active IngredientMiconazole nitrate
Dosage FormCream; Suppository
RouteVaginal
Strength200mg; 4%
Market StatusOver the Counter; Prescription
CompanyInsight Pharms

18 of 22  
Drug NameMonistat 3 combination pack
Active IngredientMiconazole nitrate
Dosage FormCream
RouteTopical, vaginal
Strength2%,4%
Market StatusOver the Counter
CompanyInsight Pharms

19 of 22  
Drug NameMonistat 7
Drug LabelORAVIG (miconazole) buccal tablets are applied topically to the gum once daily and release miconazole as the buccal tablet gradually dissolves [ see Clinical Pharmacology (12.3)].Miconazole is an imidazole antifungal agent and is described chemically...
Active IngredientMiconazole nitrate
Dosage FormCream; Suppository
RouteVaginal
Strength100mg; 2%
Market StatusOver the Counter
CompanyInsight Pharms

20 of 22  
Drug NameM-zole 3 combination pack
PubMed HealthMiconazole
Drug ClassesAntifungal, Imidazole
Active IngredientMiconazole nitrate
Dosage FormCream, suppository
RouteTopical, vaginal
Strength2%,200mg
Market StatusOver the Counter
CompanyActavis Mid Atlantic

21 of 22  
Drug NameOravig
Active IngredientMiconazole
Dosage FormTablet
RouteBuccal
Strength50mg
Market StatusPrescription
CompanyBioalliance Pharma

22 of 22  
Drug NameVusion
Active Ingredientpetrolatum, white; Miconazole nitrate; zinc oxide
Dosage FormOintment
RouteTopical
Strength15%; 81.35%; 0.25%
Market StatusPrescription
CompanyDelcor Asset

4.2 Drug Indication

Miconazole is indicated for the local treatment of oropharyngeal candidiasis in adult patients and for the adjunctive treatment of diaper dermatitis complicated by candidiasis in immunocompetent patients aged four weeks and older. Miconazole is available as both a suppository and cream for the treatment of vaginal yeast infections and the relief of associated vulvar itching and irritation. Lastly, miconazole cream is effective in treating athlete's foot (tinea pedis), jock itch (tinea cruris), ringworm infections (tinea corporis), pityriasis (formerly tinea) versicolor, and cutaneous candidiasis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Miconazole is an azole antifungal that functions primarily through inhibition of a specific demethylase within the CYP450 complex. As miconazole is typically applied topically and is minimally absorbed into the systemic circulation following application, the majority of patient reactions are limited to hypersensitivity and cases of anaphylaxis. Patients using intravaginal miconazole products are advised not to rely on contraceptives to prevent pregnancy and sexually transmitted infections, as well as not to use tampons concurrently.


5.2 MeSH Pharmacological Classification

Cytochrome P-450 CYP3A Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)


Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


14-alpha Demethylase Inhibitors

Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)


Cytochrome P-450 CYP2C9 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C9. (See all compounds classified as Cytochrome P-450 CYP2C9 Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MICONAZOLE
5.3.2 FDA UNII
7NNO0D7S5M
5.3.3 Pharmacological Classes
Azoles [CS]; Azole Antifungal [EPC]
5.4 ATC Code

D01AC02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB09 - Miconazole


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AC - Imidazole derivatives

A07AC01 - Miconazole


D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC02 - Miconazole


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF04 - Miconazole


J - Antiinfectives for systemic use

J02 - Antimycotics for systemic use

J02A - Antimycotics for systemic use

J02AB - Imidazole derivatives

J02AB01 - Miconazole


S - Sensory organs

S02 - Otologicals

S02A - Antiinfectives

S02AA - Antiinfectives

S02AA13 - Miconazole


5.5 Absorption, Distribution and Excretion

Absorption

Miconazole given to healthy volunteers as a single 50 mg oral tablet produced a mean Cmax of 15.1 16.2 mcg/mL, a mean AUC0-24 of 55.2 35.1 mcg\*h/mL, and a median Tmax of 7 hours (range 2.0-24.1). In these patients measurable plasma concentrations ranged from 0.5 to 0.83 mcg/mL. Topical miconazole is absorbed poorly into the systemic circulation. In pediatric patients aged 1-21 months given multiple topical applications of miconazole ointment for seven days, the plasma miconazole concentration was less than 0.5 ng/mL in 88% of the patients, with the remaining patients having a concentration of 0.57 and 0.58 ng/mL, respectively. Similarly, patients. administered with a vaginal 1200 mg ovule had a mean Cmax of 10.71 ng/mL, mean Tmax of 18.4 hours, and mean AUC0-96 of 477.3 ng\*h/mL.


Route of Elimination

Miconazole is excreted through both urine and feces; less than 1% of unchanged miconazole is recovered in urine.


Volume of Distribution

A 1200 mg miconazole vaginal suppository resulted in a calculated apparent volume of distribution of 95 546 L while a 100 mg vaginal cream yielded an apparent volume of distribution of 10 911L.


5.6 Metabolism/Metabolites

Miconazole is metabolized in the liver and does not give rise to any active metabolites.


5.7 Biological Half-Life

Miconazole has a terminal half-life of 24 hours.


5.8 Mechanism of Action

Miconazole is an azole antifungal used to treat a variety of conditions, including those caused by _Candida_ overgrowth. Unique among the azoles, miconazole is thought to act through three main mechanisms. The primary mechanism of action is through inhibition of the CYP450 14-lanosterol demethylase enzyme, which results in altered ergosterol production and impaired cell membrane composition and permeability, which in turn leads to cation, phosphate, and low molecular weight protein leakage. In addition, miconazole inhibits fungal peroxidase and catalase while not affecting NADH oxidase activity, leading to increased production of reactive oxygen species (ROS). Increased intracellular ROS leads to downstream pleiotropic effects and eventual apoptosis. Lastly, likely as a result of lanosterol demethylation inhibition, miconazole causes a rise in intracellular levels of farnesol. This molecule participates in quorum sensing in _Candida_, preventing the transition from yeast to mycelial forms and thereby the formation of biofilms, which are more resistant to antibiotics. In addition, farnesol is an inhibitor of drug efflux ABC transporters, namely _Candida_ CaCdr1p and CaCdr2p, which may additionally contribute to increased effectiveness of azole drugs.